Ester molecules are polar but have no hydrogen atom attached directly to an oxygen atom. They are therefore incapable of engaging in intermolecular hydrogen bonding with one another and thus have considerably lower boiling points than their isomeric carboxylic acids counterparts. Because ester molecules can engage in hydrogen bonding with water molecules, however, esters of low molar mass are somewhat soluble in water. Borderline solubility occurs in those molecules that have three to five carbon atoms. Table 15.4 "Physical Properties of Some Esters" lists the physical properties of some common esters.
Esters are common solvents. Ethyl acetate is used to extract organic solutes from aqueous solutions—for example, to remove caffeine from coffee. It also is used to remove nail polish and paint. Cellulose nitrate is dissolved in ethyl acetate and butyl acetate to form lacquers. The solvent evaporates as the lacquer “dries,” leaving a thin film on the surface. High boiling esters are used as softeners (plasticizers) for brittle plastics.
Table 15.4 Physical Properties of Some Esters
|Condensed Structural Formula||Name||Molar Mass||Melting Point (°C)||Boiling Point (°C)||Aroma|
Which compound has the higher boiling point—CH3CH2CH2CH2OH or CH3COOCH3? Explain.
Which compound is more soluble in water—methyl butyrate or butyric acid? Explain.
CH3CH2CH2CH2OH because there is intermolecular hydrogen bonding (There is no intermolecular hydrogen bonding in CH3COOCH3.)
butyric acid because of hydrogen bonding with water
Which compound has the higher boiling point—CH3CH2CH2COOH or CH3CH2CH2COOCH3? Explain.
Which compound is more soluble in water—methyl acetate or octyl acetate? Explain.
CH3CH2CH2COOH because there is intermolecular hydrogen bonding (There is no intermolecular hydrogen bonding in CH3CH2COOCH3.)